Morpholine → Methyl 3-(morpholin-4-yl)phenylacetate

HRID 1017565

反応式

HRID 1017565 の反応式
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:13]1([C:2]2[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

参加物

7

反応物 3

HCID 8083MorpholineHCID 634876Binap, (A+-)-HCID 11746402Methyl 2-(3-bromophenyl)acetate

生成物 1

HCID 18403524Methyl 3-(morpholin-4-yl)phenylacetate収率 23%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

A round bottom flasked flushed with argon was charged with methyl 3-bromophenyl-acetate (2.29 g, 10 mmol) (prepared from 3-bromophenylacetic acid as described in example 2, step 1), morpholine (1.05 mL, 1.2 eq.), CsCO3 (4.55 g, 1.4 eq.), Pd2(dba)3 (92 mg, 0.01 eq) and BINAP (93 mg, 0.15 eq.) in toluene (20 mL). The resulting mixture was heated at 100° C. overnight and then diluted with diethyl ether (120 mL). The precipitates were filtered through a Celite pad and the filtrate was concentrated and purified on a silica-gel column with 20% EtOAc in hexane to give methyl 3-(morpholin-4-yl)phenylacetate (0.55 g, 23%).

後処理

  1. customA round bottom flasked flushed with argon
  2. filtrationThe precipitates were filtered through a Celite pad
  3. concentrationthe filtrate was concentrated
  4. custompurified on a silica-gel column with 20% EtOAc in hexane

出典と根拠

ORDレコード
ord-d77f8454ac2a429885df267293caef92
出典データセット
uspto-grants-2002_11
特許番号
US06479490B2

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